Patent GB-645062-A (GB)
Title: Sulphonation products of cashew nut sheel liquid and the like
Filed: 1947-07-28
Abstract: Cardonal, urushiol or a phenol of cashew or marking nut shell liquid is converted into an alkyl or aryl ether and the product sulphonated. Preferred ethers are the alkyl ethers with 1-5 carbon atoms in the alkyl group.  The products are probably mixtures of mono- and disulphonic acids, and may be converted into their ammonium, sodium, potassium, calcium or other metal salts.  Examples show the sulphonation of the ethyl and propyl ethers of cardanol and the ethyl ether of cashew nut shell liquid.  The Specification as open to inspection under Sect. 91 refers generally to the sulphonation of phenols containing unsaturated side-chains, and states that concurrent polymerization may be prevented in other ways than by etherification, viz: (1) hydrogenation of the side chain; (2) hydrogenation and etherification in either order; (3) condensation with a phenol free from unsaturated side-chains or an ether thereof, as in Specification 627,919; (4) as in (3) using a mixture of two or more phenols; (5) etherification combined with (3) or (4) in either order; or (6) acetylation of the product of (3) or (4). Examples are given of the condensation of cardanol with phenol, o-allyl-phenol with phenol, and of cashew nut shell liquid with a mixture of phenol and cresols.  Other reactants referred to are allyl-phenol and o-cresol, dihydroxy urushiol and o-cresol, and cardanol and allyl-phenol.  The di-phenols obtained may be represented by the general formula R1-O-Ar-(CH2)m-CH(ArOR2)-CH2R o R1-O-Ar-(CH2)m-CH(OAr)-CH2R, where R, R1 and R2 are hydrogen or hydrocarbon radicals, m is zero or an integer and each aryl nucleus can be benzene, naphthalene or anthracene and may carry alkyl, hydroxy or alkoxy substituents.  The di-phenols are usually obtained by using sulphuric acid as the condensing agent, and need not be isolated, more sulphuric acid being added and the temperature raised to effect sulphonation.  The products are usually mixtures, and if an excess of the simple phenol is used in the condensation, the corresponding sulphonic acid(s) will be present in the product, e.g. phenol- and cresol-sulphonic acids.  Examples show the sulphonation of (1) hydrogenated cardanol; (2) the ethyl ether of hydrogenated cardonol; (3) the condensation product of cardanol and phenol; (4) the condensation product of o-allyl-phenol and phenol; and (5) the condensation product of cashew nut shell liquid and a mixture of phenol and cresols.  Sodium, ammonium, calcium and other metal salts of the products may be prepared. This subject-matter does not appear in the Specification as accepted.ALSO:Compounds useful as wetting agents and detergents for textiles are obtained from cardanol, a phenol of cashew or marking nut shell liquid or urushiol, by converting the phenol into an alkyl or aryl ether and sulphonating the product.  Preferred ethers are the alkyl ethers with 1-5 carbon atoms in the alkyl group.  The products are probably mixtures of mono- and di-sulphonic acids, and may be converted into their ammonium, sodium, potassium, calcium or other metal salts.  They may be used in conjunction with other sulphonic acids or their salts, e.g. those of phenol and cresols.  In the Specification as open to inspection under Sect. 91 the sulphonic acids may be derived from any phenol with an unsaturated side-chain which has been converted into a derivative in one of the following ways: (1) etherification as above; (2) hydrogenation of the side chain; (3) hydrogenation and etherification; (4) condensation with a phenol free from unsaturated side chains or an ether thereof as in Specification 627,919, or (5) etherification or acetylation combined with (4).  In the case of (4) and (5), excess of the simple phenol may be used, the corresponding sulphonic acid(s) being present in the product, e.g. phenol- and cresol-sulphonic acids.  The products are sulphonic acids (usually mixtures) of compounds of the general formula R1-O-Ar-(CH2)m-CH(Ar)R2)-CH2R or R1-O-Ar-(CH2)m-CH(oAr)-CH2R, where R, R1 and R2 are hydrogen or hydrocarbon radicals, m is zero or an integer and each aryl nucleus can be benzene, naphthalene or anthracene and may carry alkyl, hydroxy or alkoxy substituents. Examples show the sulphonic acids of (1) hydrogenated cardanol; (2) the ethyl ether of hydrogenated cardanol; (3) the condensation product of cardanol and phenol; (4) the condensation product of o-allyl-phenol and phenol, and (5) the condensation product of cashew nut shell liquid and a mixture of phenols and cresols.  Sodium, ammonium, calcium and other metal salts of the products may be prepared.  This subject-matter does not appear in the Specification as accepted.